p-Toluenesulfonic acid monohydrate → HCID 178499180, compound

HRID 467647Notes

Reaction equation

HRID 467647 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([OH:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].O.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:13][O:10][C:9]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=1)=[O:11]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178524956HCID 178524956, compound

Product 1

HCID 178499180HCID 178499180, compoundYield 1,771.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (5 g, 31.8 mmol) in dry MeOH (60 ml) was added freshly crystallized p-toluenesulphonic acid monohydrate (300 mg, 1.6 mmol). The reaction mixture was heated at 65° C. for 16 hrs. MeOH was removed in vacuo. The residue was taken up with saturated aqueous NaHCO3 solution (15 ml) and extracted with EtOAc. The combined organic layers were washed with water, and then with brine, dried (Na2SO4), filtered, and evaporated. The crude product was purified by column chromatography over silica gel using 30% EtOAc/hexane) to provide the title compound as white solid (4.85 g, 89%).

Workup

  1. customMeOH was removed in vacuo
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialwith brine, dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography over silica gel using 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-30c061d774e34a80948e3e796b79fb24
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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